If you're looking to make an unforgettable getaway, let Winston Churchill, Geronimo, and the slave who mailed himself to freedom show you the way.

1. How to Become the Subject of a Country Ballad

Christopher Daniel Gay is nicknamed Little Houdini for a reason: The 5'5" Tennessee native knows how to make 18-wheelers and construction equipment vanish into thin air. More impressively, he knows how to perform such disappearing acts in police custody. But Gay is more than just a master thief and escape artist; he's also a loving son.

In 2005, Gay broke out of a Nashville jail to visit his ailing father. Two years later, he fled from the authorities to see his dying mother. This time, Gay was being transported to a jail in Alabama for stealing an RV. Somehow, he freed himself from a full set of shackles (on his hands, feet, and waist!) and gave two policemen the slip at a South Carolina rest stop. He then stole a pickup truck, drove 300 miles, hot-wired an 18-wheeler, and drove another 100 miles to a town just north of Nashville. The police were hot on his trail, but Gay refused to pull over until he reached his mother's house, where he drove the big rig onto her front lawn and fled into the woods.

But the story doesn't end there. Gay then headed to Nashville and stole country singer Crystal Gayle's tour bus. He drove the bus to a NASCAR race in Lakeland, Florida, where he told the track manager that he was there to pick up Tony Stewart, the legendary race car driver.

When authorities became suspicious, Gay abandoned the tour bus and fled. The details of the escapade are immortalized in Tim O'Brien's 2007 hit country song "The Ballad of Christopher Daniel Gay."

Last February, Gay was arrested once again in Florida. But he escaped as police were transporting him back to Tennessee. Despite locking down the surrounding area and searching for Gay with helicopters and bloodhounds, Little Houdini worked his magic on a big rig and took flight yet again.

Gay and his 18-wheeler were finally apprehended on March 16, 2008, near a Wal-Mart in Lakeland, Florida. A spokeswoman for the Polk County sheriff's department told journalists, "He is being treated as an escape risk." You can say that again.

2. Skydiving for Cash

On November 24, 1971, a man calling himself Dan Cooper boarded Northwest Orient Flight 305 from Portland to Seattle, carrying only a briefcase. Once in the air, he handed the stewardess a note. When she ignored the gesture, Cooper politely redrew her attention to the message. This time, she realized how serious the situation was. The note said that Cooper had a bomb in his briefcase, and that he planned on setting it off unless he received $200,000 cash and some parachutes upon landing in Seattle. After having his demands met, Cooper redirected the plane to Mexico. He also gave the pilot instructions to maintain a speed of less than 150 knots and an altitude of less than 10,000 feet, and to keep the flaps set at 15 degrees. All of this kept the plane moving slowly enough for Cooper to make a dramatic exit. With cash in hand and a parachute on his back, Cooper jumped out of the plane somewhere over the Washington-Oregon border.

To this day, Cooper's whereabouts are unknown. Authorities maintain that he probably died while leaping from the plane, but there's evidence to suggest otherwise. In 1978, hikers in Oregon (near the area where Cooper had jumped) found instructions for descending the rear stairwell of a Boeing 727. And in 1981, an 8-year-old boy discovered $5,880 that turned out to be part of Cooper's ransom money. Neither discovery is conclusive proof, but there is one more piece of evidence: In 1997, the FBI opened a posthumous investigation into Duane Weber, an antiques dealer in Florida who made a deathbed admission that he was Dan Cooper. It turns out that Weber had a criminal record, serving six prison terms for burglary and forgery, and that he'd received military training during WWII, which included skydiving.

3. Thinking Inside the Box

On March 29, 1849, a 33-year-old Virginia slave known as Henry "Box" Brown earned his middle name by mailing himself to freedom. At the time, Brown was heartbroken. His wife of 18 years and their three children had been taken away from him and sold to a slave owner in North Carolina. With little to lose, Brown convinced a white shopkeeper to seal him in a box that measured roughly 3 ft. x 2 ft. x 2 ft. and mail the package to an abolitionist in Philadelphia. The journey lasted 27 hours, and although the container was marked "This side up with care," handlers largely ignored the instructions. The box moved from wagon to railroad to steamboat to wagon to railroad to ferry to railroad and then to wagon again—all the way to Philadelphia. Incredibly, all that jostling had little effect on Brown's manners. When abolitionists pried open the delivery and Brown emerged from the box, his first words were allegedly, "How do you do, gentlemen?"

4. Geronimo's Magic

If Dan Cooper had yelled "Geronimo!" when he jumped from that plane in 1971, it would have been appropriate, as the Apache renegade was a great escape artist in his own right. In 1851, after Mexican soldiers killed his mother, one of his wives, and his three children, Geronimo went on a rampage. The 22-year-old Indian warrior quickly became legendary for his fearless method of attack. He would appear out of nowhere—wielding only a knife—and run head-first through gunfire to stab his enemies. Seemingly impervious to bullets, Geronimo killed hundreds of troops and settlers across northern Mexico and the American Southwest.

After five years of guerrilla warfare, some 10,000 U.S. and Mexican troops began pursuing Geronimo. And yet, he still managed to evade them with his near-supernatural ability to vanish into the terrain. Indeed, the Apache believed he had special powers—walking without leaving tracks, reading minds, and moving objects with his thoughts. In fact, legend has it that Geronimo once led his band of Apaches into a cave in the Robledo Mountains of New Mexico. The American army was at his heels, and as soon as Geronimo entered the cave, troops fanned out and blocked the only other exit. They thought they had him cornered. But a few days later, Geronimo and his followers appeared miles away from the cave. Hundreds of historians, geologists, and archaeologists have since combed the site to figure out how Geronimo made his incredible escape, but to this day, experts are baffled.

5. Winston Churchill's Prison Break

In 1899, Great Britain found itself in South Africa warring with the Boers—South Africans of Dutch descent. One of the British journalists covering the war was an adventurous 24-year-old named Winston Churchill, who loved combat so much that he became a war correspondent after his discharge from the army. On November 15, the Boers captured Churchill and threw him into a POW camp in Pretoria. Immediately, he began closely monitoring the guards and realized that there was a gap in their routine when no one was watching the 10-ft. wall surrounding his building. So, Churchill decided to make a break for it. But first, he needed to settle some accounts. Being the gentleman that he was, he paid his bill with the Boer shopkeeper who'd sold him tobacco, and he wrote a note of thanks and apology to the Boer Minister of War, who'd also befriended him. Then he scaled the wall.

Upon escaping, Churchill ran to a nearby villa, where he waited until he was able to hop on a passing train. For several more days, he followed the rail lines, sleeping in ditches, stealing food where he could, and fishing newspapers out of trash bins to read about the manhunt pursuing him. Six days later, Churchill made the last leg of his journey when he crept onto a train headed for the Portuguese colony at Delagoa Bay. The ride took him 250 miles east to the Mozambique coast, where he crossed the border into freedom. Churchill's daring escape did wonders for his name. It made him a celebrity in England and helped launch his political career.

6. The Dalai Lama Makes a Break for It

In 1959, as the Chinese cracked down on Tibetan rebels, Mao Zedong set his sights on the Dalai Lama, and it became clear the young Buddhist leader was in danger. Not knowing the best time to flee, the Lama started consulting the Oracle—a fellow monk who reveals prophesies while in trance. For several days in a row, the Oracle told the Lama to stay put. But that changed on March 17. As riots busied the Chinese authorities, the Oracle suddenly insisted that the Lama get moving. Disguised as an ordinary Tibetan, the spiritual leader snuck out of the ancestral palace without alerting anyone. Once in the countryside, he met up with his family and top religious officials, and together, they headed to India through the Himalayas.

It wasn't until two days later that the Chinese government realized the Dalai Lama had flown the coop. When they figured out what had happened, they immediately closed the Tibetan border and dispatched 50,000 troops to stop the famous Buddhist. But it was no use. Many of the mountain passes were only known to Tibetan mountain guides who would rather have died than betray their spiritual leader. Meanwhile, heavy cloud cover prevented the Chinese air force from performing aerial reconnaissance. Two weeks later, after trekking through the rugged mountain range and negotiating the treacherous Brahmaputra River, the Dalai Lama surfaced at Tawang Monastery, 50 miles inside the Indian border.

7. The Cold War and the Hot Air Balloon

After watching a TV show about the history of hot air balloons, two friends living in East Germany, Hans Strelczyk and Gunter Wetzel, had a brilliant idea: What if they put their families in a hot air balloon and simply flew over the Berlin Wall? Capitalizing on Strelczyk's skills as a mechanic and Wetzel's as a mason, the pair built an engine out of propane gas cylinders and constructed a balloon out of taffeta. However, as the plans moved forward, Wetzel's wife got cold feet, and the Strelczyks decided to go it alone. On July 4, 1979, the family launched the balloon from a meadow about 25 miles from Berlin. But damp conditions squelched the hot-air burner after only a few minutes. They made a hasty landing in East Germany, where the border guards spotted them. The Strelczyks managed to escape, but East Germany's brutal secret police, the Stasi, was now wise to their plan.

Terrified of being discovered, both families set to work again. The men built a bigger, sturdier burner, and the women stitched together 60 pieces of canvas and bedsheets to make the balloon. On the night of September 16, with Stasi detectives hot on their trail, the two families reached the launch site, inflated the balloon, and took to the air. Because the balloon had no basket, the two men, two women, and four children all clung to a small metal platform as the device climbed to 8,000 feet. After 30 minutes, they landed, unsure of which country they were in. They eventually spotted a police officer, who confirmed they were in West Germany. The two families became instant heroes around the world, and their balloon was seen as a symbol of freedom.

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The article above, written by Erik Sass, is reprinted with permission from the Jul/Aug 2009 issue of mental_floss magazine. Get a subscription and never miss an issue!